Sodium maleonitriledithiolate

Sodium maleonitriledithiolate
Names
	IUPAC name sodium cis-1,2-dicyano-1,2-ethylenedithiolate
	Other names sodium mnt sodium maleonitriledithiolate
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	5013443 ;
PubChem CID	6523934;
	InChI InChI=1S/C4H2N2S2.2Na/c5-1-3(7)4(8)2-6;;/h7-8H;;/q;2+1/p-2/b4-3+;; Key: UIEQIOFOWZBELJ-CZEFNJPISA-L ; InChI=1/C4H2N2S2.2Na/c5-1-3(7)4(8)2-6;;/h7-8H;;/q;2+1/p-2/b4-3+;; Key: UIEQIOFOWZBELJ-YWCBZGCUBZ;
	SMILES [Na+].[Na+].[S-]/C(C#N)=C(/[S-])C#N;
Properties
Chemical formula	C4N2Na2S2
Molar mass	186.17 g/mol
Appearance	yellow solid
Solubility in ethanol, DMF	Soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Sodium maleonitriledithiolate is the chemical compound described by the formula Na₂S₂C₂(CN)₂. The name refers to the cis compound, structurally related to maleonitrile ((CHCN)₂). Maleonitriledithiolate is often abbreviated mnt. It is a "dithiolene", i.e. a chelating alkene-1,2-dithiolate. It is a prototypical non-innocent ligand in coordination chemistry. Several complexes are known, such as [Ni(mnt)₂]²⁻.[1]^:143–146

Sample of (Et₄N)₂Ni(mnt)₂.

The salt is synthesized by treating carbon disulfide with sodium cyanide to give the cyanodithioformate salt, which eliminates elemental sulfur in aqueous solution:[2]

2 NaCN + 2 CS₂ → Na₂S₂C₂(CN)₂ + 1/4 S₈

The compound was first described by Bähr and Schleitzer 1958.[3]

References

Day, P. and Coronado, E. (2004) Molecular Materials Combining Magnetic and Conducting Properties, in Magnetism: Molecules to Materials V (eds J. S. Miller and M. Drillon), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527604383.ch4
R. H. Holm, A. Davison "Metal Complexes Derived from cis-1,2-Dicyano-1,2-Ethylenedithiolate and Bis(trifluoromethyl)-1,2-Dithiete" Inorganic Syntheses 1967, volume X, pp.8-26.
G. Bähr and G. Schleitzer (1957). "Beiträge zur Chemie des Schwefelkohlenstoffs und Selenkohlenstoffs, II. Die Kondensierende Spontan-Entschwefelung von Salzen und Estern der Cyan-Dithioameisensäure. Freie Cyan-Dithioameisensäure". Chemische Berichte. 90 (3): 438–443. doi:10.1002/cber.19570900322.

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[1] Day, P. and Coronado, E. (2004) Molecular Materials Combining Magnetic and Conducting Properties, in Magnetism: Molecules to Materials V (eds J. S. Miller and M. Drillon), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527604383.ch4

[2] R. H. Holm, A. Davison "Metal Complexes Derived from cis-1,2-Dicyano-1,2-Ethylenedithiolate and Bis(trifluoromethyl)-1,2-Dithiete" Inorganic Syntheses 1967, volume X, pp.8-26.

[3] G. Bähr and G. Schleitzer (1957). "Beiträge zur Chemie des Schwefelkohlenstoffs und Selenkohlenstoffs, II. Die Kondensierende Spontan-Entschwefelung von Salzen und Estern der Cyan-Dithioameisensäure. Freie Cyan-Dithioameisensäure". Chemische Berichte. 90 (3): 438–443. doi:10.1002/cber.19570900322.